Novel Two-Step Synthesis of N-Alkylated 2,3-Diaryl-4-quinolones

Abstract

A library of 18 polysubstituted 4-quinolones was conveniently prepared via simple and practical protocol involving N-alkylation of 2-(3-oxoindolin-2-yl)acetonitriles and following NaH-induced ring expansion. The current two-step approach provides feasible access to a subclass of N-protected C3-aryl-substituted 2-phenyl-4-quinolones starting with or just one step away from commercially available 2-arylindoles and nitrostyrenes.

Key words

4-quinolones - indoles - rearrangement - cascade transformations - nitroalkenes

Publication History

Received: 11 September 2023

Accepted after revision: 07 November 2023

Article published online:
06 December 2023

• References

• 1 Bisacchi GS. J. Med. Chem. 2015; 58: 4874
• 2 Suaifan GA. R. Y, Mohammed AA. M. Bioorg. Med. Chem. 2019; 27: 3005
• 3 Dhiman P, Arora N, Thanikachalam PV, Monga V. Bioorg. Chem. 2019; 92: 103291
• 4 Dube PS, Legoabe LJ, Beteck RM. Mol. Divers. 2023; 27: 1501
• 5 Dine I, Mulugeta E, Melaku Y, Belete M. RSC Adv. 2023; 13: 8657
• 6 Ghosh S, Bishayee K, Khuda-Bukhsh AR. Phyther. Res. 2014; 28: 1153
• 7 Shen L, Chen Y.-L, Huang C.-C, Shyu Y.-C, Seftor RE. B, Seftor EA, Hendrix MJ. C, Chien D.-S, Chu Y.-W. Pathol. Oncol. Res. 2023; 29: 1611038
• 8 Nakamura S, Kozuka M, Bastow KF, Tokuda H, Nishino H, Suzuki M, Tatsuzaki J, Morris Natschke SL, Kuo S.-C, Lee K.-H. Bioorg. Med. Chem. 2005; 13: 4396
• 9 Lai Y.-Y, Huang L.-J, Lee K.-H, Xiao Z, Bastow KF, Yamori T, Kuo S.-C. Bioorg. Med. Chem. 2005; 13: 265
• 10 Li L, Wang H, Kuo S, Wu T, Mauger A, Lin CM, Hamel E, Lee K.-H. J. Med. Chem. 1994; 37: 3400
• 11 Hamel E, Lin CM, Plowman J, Wang H.-K, Lee K.-H, Paull KD. Biochem. Pharmacol. 1996; 51: 53
• 12 Kuo SC, Lee HZ, Juang JP, Lin YT, Wu TS, Chang JJ, Lednicer D, Paull KD, Lin CM, Hamel E, Lee KH. J. Med. Chem. 1993; 36: 1146
• 13 Boteva AA, Krasnykh OP. Chem. Heterocycl. Compd. 2009; 45: 757
• 14 Aksenov AV, Aksenov DA, Aksenov NA, Aleksandrova EV, Rubin M. J. Org. Chem. 2019; 84: 12420
• 15 Jun W, Yumin S, Heng Y. Future Med. Chem. 2023; 15: 555
• 16 Sharma V, Das R, Kumar Mehta D, Gupta S, Venugopala KN, Mailavaram R, Nair AB, Shakya AK, Kishore Deb P. Bioorg. Med. Chem. 2022; 59: 116674
• 17 Singh G, Devi V, Monga V. ChemistrySelect 2020; 5: 14100
• 18 Shen C, Wang A, Xu J, An Z, Loh KY, Zhang P, Liu X. Chem 2019; 5: 1059
• 19 Ghosh P, Das S. Eur. J. Org. Chem. 2019; 4466
• 20 Silva VL. M, Silva AM. S. Molecules 2019; 24: 228
• 21 Mphahlele MJ, Nwamadi MS, Mabeta P. J. Heterocycl. Chem. 2006; 43: 255
• 22 Mphahlele MJ, Mtshemla V. J. Chem. Res. 2008; 437
• 23 Hu W, Lin JP, Song LR, Long YQ. Org. Lett. 2015; 17: 1268
• 24 Shao J, Huang X, Hong X, Liu B, Xu B. Synthesis 2012; 44: 1798
• 25 Bandatmakuru S, Arava V. SynOpen 2018; 2: 285
• 26 Wang D, Sun P, Jia P, Peng J, Yue Y, Chen C. Synthesis 2017; 49: 4309
• 27 Zhao T, Xu B. Org. Lett. 2010; 12: 212
• 28 Fei X.-D, Zhou Z, Li W, Zhu Y.-M, Shen J.-K. Eur. J. Org. Chem. 2012; 3001
• 29 Jones CP, Anderson KW, Buchwald SL. J. Org. Chem. 2007; 72: 7968
• 30 Ferretti F, Fouad MA, Abbo C, Ragaini F. Molecules 2023; 28: 5424
• 31 Miliutina M, Ejaz SA, Khan SU, Iaroshenko VO, Villinger A, Iqbal J, Langer P. Eur. J. Med. Chem. 2017; 126: 408
• 32 Yang F, Wang X, Zhao W, Yu F, Yu Z. ACS Omega 2021; 6: 34044
• 33 Hong WD, Gibbons PD, Leung SC, Amewu R, Stocks PA, Stachulski A, Horta P, Cristiano ML. S, Shone AE, Moss D, Ardrey A, Sharma R, Warman AJ, Bedingfield PT. P, Fisher NE, Aljayyoussi G, Mead S, Caws M, Berry NG, Ward SA, Biagini GA, O’Neill PM, Nixon GL. J. Med. Chem. 2017; 60: 3703
• 34 Ritu, Kumar S, Chauhan P, Jain N. Org. Biomol. Chem. 2021; 19: 4585
• 35 Hessian KO, Flynn BL. Org. Lett. 2006; 8: 243
• 36 Ko T.-C, Hour M.-J, Lien J.-C, Teng C.-M, Lee K.-H, Kuo S.-C, Huang L.-J. Bioorg. Med. Chem. Lett. 2001; 11: 279
• 37 Hadjeri M, Mariotte A.-M, Boumendjel A. Chem. Pharm. Bull. 2001; 49: 1352
• 38 Ravi M, Chauhan P, Kant R, Shukla SK, Yadav PP. J. Org. Chem. 2015; 80: 5369
• 39 Shi Y, Xing H, Huang T, Liu X, Chen J, Guo X, Li G.-B, Wu Y. Chem. Commun. 2020; 56: 1585
• 40 Liu L, Li J, Dai W, Gao F, Chen K, Zhou Y, Liu H. Molecules 2020; 25: 268
• 41 Liu X, Chen J, Yang C, Wu Z, Li Z, Shi Y, Huang T, Yang Z, Wu Y. Org. Lett. 2021; 23: 6831
• 42 Wu X, Zheng L.-L, Zhao L.-P, Zhu C.-F, Li Y.-G. Chem. Commun. 2019; 55: 14769
• 43 Liu J, Ba D, Lv W, Chen Y, Zhao Z, Cheng G. Adv. Synth. Catal. 2020; 362: 213
• 44 Zhang S, Wu C, Zhang Z, Wang T. Org. Lett. 2019; 21: 9995
• 45 Santhosh Reddy R, Lagishetti C, Kiran IN. C, You H, He Y. Org. Lett. 2016; 18: 3818
• 46 Ji X, Li D, Wang Z, Tan M, Huang H, Deng G.-J. Asian J. Org. Chem. 2018; 7: 711
• 47 Ma H, Zhou X, Wei D, Cao J, Shi C, Fan Y, Huang G. Chem. Asian J. 2016; 11: 2829
• 48 Yoshino Y, Kurahashi T, Matsubara S. J. Am. Chem. Soc. 2009; 131: 7494
• 49 Lee SB, Jang Y, Ahn J, Chun S, Oh D.-C, Hong S. Org. Lett. 2020; 22: 8382
• 50 Romek A, Opatz T. Eur. J. Org. Chem. 2010; 5841
• 51 Sardar B, Pal D, Sarmah R, Srimani D. Chem. Commun. 2023; 59: 9267
• 52 Aksenov AV, Aksenov NA, Aksenov DA, Khamraev VF, Rubin M. Chem. Commun. 2018; 54: 13260
• 53 Aksenov AV, Aksenov DA, Arutiunov NA, Aksenov NA, Aleksandrova EV, Zhao Z, Du L, Kornienko A, Rubin M. J. Org. Chem. 2019; 84: 7123
• 54 Aksenov AV, Aksenov NA, Aleksandrova EV, Aksenov DA, Grishin IY, Sorokina EA, Wenger A, Rubin M. Molecules 2021; 26: 6132
• 55 Aksenov AV, Aleksandrova EV, Aksenov DA, Aksenova AA, Aksenov NA, Nobi MA, Rubin M. J. Org. Chem. 2022; 87: 1434
• 56 Xu F, Smith MW. Synlett 2023; 34: 1539
• 57 Xu F, Smith MW. Chem. Sci. 2021; 12: 13756
• 58 Shimizu M, Imazato H, Mizota I, Zhu Y. RSC Adv. 2019; 9: 17341
• 59 Barkenbus C, Owen J. J. Am. Chem. Soc. 1934; 56: 1204
• 60 Guijarro D, Guillena G, Mancheño B, Yus M. Tetrahedron 1994; 50: 3427
• 61 CCDC 2288671 (3a) and 2292334 (3d) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures